Jeff Winston is 43 and stuck in a loveless marriage and dead end job. At 1:06pm on October 18, 1988, he has a sudden, fatal heart attack and the next moment finds himself 18 in his college dorm room in May of 1963. He makes a killer bet on who he already knows will win the Kentucky Derby and uses his winnings and knowledge of the future to create a Fortune 500 company. By 1988 he is wealthy and powerful... and on October 18, 1988 he suffers another fatal heart attack, waking up in 1963 again.

Yep, he's stuck in a 25 year "Groundhog Day" Loop. Each time he loops back though, he's a little further along his original timeline. He meets Pamela, a woman who is also stuck in the loop. Together they find some stability in their lives and seek out others who may be looping themselves. What's going to happen when Jeff's loop back point and the day in 1988 eventually meet?

Tropes Present in this work:

Alternate History: Given the length of time this character loops, each "replay" is one of these by differing degrees.

Driven to Suicide: Jeff's college roommate, Martin, committed suicide in the original timeline.

Do Well, but Not Perfect: Jeff becomes a billionaire his first replay, but on subsequent runs tries to simply make enough to be comfortable and not draw attention to himself.

Foreshadowing: A different shooter kills JFK after Jeff's intervention, setting up the quasi-government agency that hold Jeff and Pamela prisoner a few replays later, trying to extract information from them.

Free-Love Future: Jeff's girlfriend in 1963 wants to help him get off but remain a Technical Virgin. She is horribly offended when he suggests having sex and asks to be driven home. Jeff muses to himself that things are a little more loose in the "future" time of the 1980's.

In Spite of a Nail: Jeff tries to save JFK by getting Lee Harvey Oswald on the Secret Service's radar. JFK is assassinated anyway.

It's a Small World After All: Averted. There are relatively few replayers, and they only notice each other when one of them affects the timeline once - producing the movie Starsea.

The Jail Bait Wait: (Also see Legal Jailbait, below) The first time Jeff and Pam replay together, Pam is in her mid-teens. Pam skews late, and Jeff causes some uncomfortable moments with Pam's family before Pam arrives for her replay. Once she replays they spend time together on their "dates to the movies", by going to a hotel instead since they both can recite the plot of any movie playing from memory.

Last Stand: For one replay, Jeff orders a staff of doctors and medical equipment to stand by to stop the heart attack that sends him back every October 18, 1988. The doctors are confused that an otherwise healthy man is so worried - but the heart attack hits all the same and despite the doctor's efforts he's sent back again.

Legal Jailbait: Jeff replays to his early 20's while Pam is 14. This doesn't stop them from romance.

The Omniscient: Frank feels this way about Jeff after Jeff proves right over and over. It gets to be a little too much for him when he discovers Jeff was in Dallas a week before JFK is shot, so he cuts off ties with Jeff.

Point of View: Almost the entire book directly follows Jeff, save for a few times it switches to Pamela and the Epilogue.

Serial Killer: One replayer is certainly making the most of his repeats.

Set Right What Once Went Wrong: Jeff always ensures that Martin is wealthy enough to keep him from committing suicide. Also the replay where he has a healthy relationship with Linda.

Shown Their Work: Grimwood did a good job of researching the time period, from seeing which races and stocks would give the highest returns, to seeing when certain technology was available but hadn't taken off yet (ie, there were commercially available but expensive word processors and videotape machines available in the 1970's - long before both became popular in the 1980's )

That Was Not A Dream: Invoked during Jeff's first replay. Also, after Jeff awakens from his final replay at a point following the heart attack, he needs to call Pamela to verify that their loops actually occurred.

Pamela does this as well; during one replay she creates a hugely successful film called Starsea, recruiting two unknowns to helm the project—director Steven Spielberg and special effects producer George Lucas.

Twenty Minutes into the Future: Jeff's heart attack happens in 1988, but the book was published in 1986 - two years before 1988. The most up-to-date event covered is The Space Shuttle Challenger disaster, but the author remains purposefully vague on 1987 and 1988, because they hadn't actually happened yet. While there were arguably plenty of notable events in those years, luckily there was nothing on the level of another Pearl Harbor or a 9/11.

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